An Efficient, Regioselective, Versatile Synthesis of N-Fused 2- and 3-Aminoimidazoles via Ugi-Type Multicomponent Reaction Mediated by Zirconium(IV) Chloride in Polyethylene Glycol-400

Guchhait, Sankar K.; Madaan, Chetna

doi:10.1055/s-0028-1087915

Cited by 85 publications

(36 citation statements)

References 9 publications

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“…Compounds 3 were prepared by a ZrCl 4 -catalyzed Ugi−Strecker-type multicomponent reaction of 2-aminopyridine/pyrazine with 4-bromobenzaldehyde and tertbutyl isocyanide. 18 Compounds 4 were synthesized using 5-bromo-2-aminopyridine. Pd-catalyzed Suzuki coupling of various boronic acids with compounds 3 and 4 produced imidazo[1,2-a]pyridines/pyrazines (5a−j and 6a−k), respectively, in good yields.…”

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confidence: 99%

Switch in Site of Inhibition: A Strategy for Structure-Based Discovery of Human Topoisomerase IIα Catalytic Inhibitors

Baviskar¹,

Amrutkar²,

Trivedi³

et al. 2015

ACS Med. Chem. Lett.

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A study of structure-based modulation of known ligands of hTopoIIα, an important enzyme involved in DNA processes, coupled with synthesis and in vitro assays led to the establishment of a strategy of rational switch in mode of inhibition of the enzyme's catalytic cycle. 6-Arylated derivatives of known imidazopyridine ligands were found to be selective inhibitors of hTopoIIα, while not showing TopoI inhibition and DNA binding. Interestingly, while the parent imidazopyridines acted as ATP-competitive inhibitors, arylated derivatives inhibited DNA cleavage similar to merbarone, indicating a switch in mode of inhibition from ATP-hydrolysis to the DNA-cleavage stage of catalytic cycle of the enzyme. The 6-aryl-imidazopyridines were relatively more cytotoxic than etoposide in cancer cells and less toxic to normal cells. Such unprecedented strategy will encourage research on "choicebased change" in target-specific mode of action for rapid drug discovery.

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confidence: 99%

Switch in Site of Inhibition: A Strategy for Structure-Based Discovery of Human Topoisomerase IIα Catalytic Inhibitors

Baviskar¹,

Amrutkar²,

Trivedi³

et al. 2015

ACS Med. Chem. Lett.

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“…To the best of our knowledge, the synthesis of compounds 6f, 7b, 7c, 7e-7f are new and have not been reported in the literature so far. Apart from the above mentioned reagents, in general imidazo [1,2-a]pyridines have been reported to be synthesized by different methodologies for this type of condensation reactions such as Sc(OTf)3 [38], ZnCl2 [39], MgCl2 [40], ZrCl4 [41], SnCl2·2H2O [42], HClO4 [27], AcOH [28], p-TSA [43], montmorillonite K-10 [44], cellulose sulfuric acid [26], catalyst free and solvent free reaction condi-tions [45,46]. Most of these methods have many limitations in terms of lower product yields, toxicity, longer reaction time, higher energetic reaction conditions or use of hazardous and volatile organic solvents like acetonitrile, toluene, chloroform etc.…”

Section: Resultsmentioning

confidence: 99%

Green Synthesis, Characterization and Antidiabetic Activity of 2-Substituted Aryl/Alkyl-N-Aryl/Alkyl Imidazo[1,2-a]pyridin-3-amine Derivatives

Kota¹,

Gandham²,

Sanasi³

2018

Asian J. Chem.

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Imidazo[1,2-a]pyridines containing ring junction have shown broad therapeutic properties in the drug discovery sector, such as the treatment of heart disease, migraines, digestive disease and viral disease. Imidazo[1,2-a]pyridine structure is very much prevalent in several marketed drugs viz., olprinone, zolpidem, levamisole, alpidem, zolimidine etc. The present paper describes the green synthesis of some novel imidazo[1,2-a]pyridine derivatives (6a-f/7a-f), a straight forward, isocyanide based Groebke-Blackburn-Bienayme, three component reactions in which aldehyde, 2-aminopyridine and isocyanide are condensed in presence of green parameters such as (i) ZnO nanoparticles/ZnFe2O4 nanoparticles (reusable heterogeneous catalysts), (ii) 2-methyl-tetrahydrofuran (green solvent) and (iii) microwave irradiation (energy efficiency reducing time period of the reaction). These derivatives were evaluated for antidiabetic experiments and the results revealed that most of the compounds were active towards antidiabetic property.

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“…The mild reaction conditions and the availability of the starting building blocks offer by far high levels of diversity and brevity. The reaction can be performed either under solvent-free (neat) conditions or by using different solvents such as methanol [49], toluene [50], acetonitrile [51], dimethyl sulfoxide [48], polyethylene glycol [52], ionic liquids [71] and water [53]. Furthermore, diverse catalysts were reported to accelerate the reaction.…”

Section: Variations Of the Catalyst And Solventmentioning

confidence: 99%

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

2015

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The Groebke-Blackburn-Bienaymé reaction (GBBR) is used for the one-pot synthesis of therapeutically relevant fused imidazoles bridgehead nitrogen heterocyclic compounds from readily available aldehyde, isocyanide and amidine building blocks. The reaction is driven by a wide range of catalysts and can be performed either under solvent or solvent-free conditions, or under microwave irradiation as heat source. The GBBR products can be used for the synthesis of a variety of more complex scaffolds via postmodification reactions. These include cyclization and nucleophilic substitution as well as further MCRs. The GBBR reaction has seen diverse applications in combinatorial and medicinal chemistry and its products are of great use in drug discovery. In this review, we summarize the efforts of the chemistry community in the progress and applications of GBBR since 1998. This review also includes some biological profiles and synthetic scopes of GBBR products. The component variations, postmodifications and secondary transformations will also be discussed throughout this review.

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An Efficient, Regioselective, Versatile Synthesis of N-Fused 2- and 3-Aminoimidazoles via Ugi-Type Multicomponent Reaction Mediated by Zirconium(IV) Chloride in Polyethylene Glycol-400

Cited by 85 publications

References 9 publications

Switch in Site of Inhibition: A Strategy for Structure-Based Discovery of Human Topoisomerase IIα Catalytic Inhibitors

Switch in Site of Inhibition: A Strategy for Structure-Based Discovery of Human Topoisomerase IIα Catalytic Inhibitors

Green Synthesis, Characterization and Antidiabetic Activity of 2-Substituted Aryl/Alkyl-N-Aryl/Alkyl Imidazo[1,2-a]pyridin-3-amine Derivatives

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

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